I am drafting the lease and planning to take it with me to closing, where we will be executing the document.

If you care and it bothers you, raise their rent another $500/mo for the hassle.

I’d take care of everything.

It depends on what your plans for the property are. 

My plan would be use the 401k kind of like a hard money loan where I'd acquire the property, rehab it, then refinance long term, pay off the 401k loan and get it rented.

That is the true idiots action plan for building wealth in real estate.

Cozy is notorious in holding your rent for over a week with the free plan.

You are going to get conflicting responses on this because a lot of it comes down to your plans and your tolerance for risk, which are things known only to you.

By tackling them early on, you minimize the risk of missing critical dates.In my experience, closing a deal within a specific timeframe requires meticulous planning.

We rent to plenty of S8 applicants; I've always believed the standard of care they exude is as high if not higher than "market" applicants because they'll get kicked out of the program if they don't.